Wiley Bayes on Red Teaming, Networking Fundamentals, and Breaking into Cybersecurity

Thomas hosts Wiley Bayes on the Cybersecurity Recruiter Podcast to discuss Wiley’s career path from early Linux curiosity and the US Navy into networking, systems/cloud engineering, penetration testing, and his current role as Senior Principal Red Team Operator at Dark Wolf Solutions.

Wiley explains day-to-day red teaming on DoD contracts, emphasizing long preparation cycles, payload testing against major security tools, patience, and tailoring phishing to the audience. He advises career changers to keep learning, focus on fundamentals (especially networking), troubleshooting, and scripting/programming, and to break into IT first rather than fixating on a dream cybersecurity role unless you’re exceptionally advanced.

They discuss Dark Wolf’s custom CTF-based hiring, communication skills gained from executive briefings, concerns about shortcuts and AI, and Wiley recommends OpenBSD and Peter N.M. Hansteen’s book “The Book of PF,” plus home lab tinkering.

00:00 Welcome and Golf Talk

01:27 Career Journey Intro

02:26 Early Curiosity and Navy Roots

03:17 Why Networking Matters

04:04 Red Team Day to Day

06:35 Phishing and Security Hygiene

08:09 Transitioning to Civilian Life

09:50 Hiring with Custom CTFs

11:31 Breaking In Is Harder Now

14:45 Finding Your Path in Security

17:55 Staying Relevant and Next Steps

20:39 Pentest To Architect Shift

21:25 Communication Under Pressure

23:17 Fundamentals And Hiring Quality

25:43 Stop Chasing Dream Roles

27:57 Learning Resources And Practice

28:57 Troubleshooting War Story

32:31 AI Shortcuts Vs Real Skills

34:36 Code And Scripting Matters

36:04 Books And Home Labbing

38:37 Wrap Up And Thanks

Barak Engel on Fractional CISO Life, Resilience, and Relationship-Driven Security Consulting Thomas chats with Barak Engel, founder/CEO of EAmmune and an advisor/board member across several security organizations, about his 23-year consulting journey, including creating the virtual/fractional CISO concept in 2003 and the realities of “feast or famine” work.

Barak discusses rapid context switching (and hitting his limit while serving six CISOs at once), resilience through setbacks such as the 2008 crash and Chapter 7 bankruptcy, and how reputation and long-term relationships drive EAmmune’s referral-only growth through “concentric circles” as clients change jobs.

He emphasizes transparency, accountability, avoiding short-term exploitation, delegating to strengths (including hiring a people manager), and focusing on minimizing damage rather than preventing all mistakes. Book recommendations include Anthony de Mello’s "Awareness," Malcolm Gladwell’s "Blink," and "The Hitchhiker’s Guide to the Galaxy," plus Barak’s book "The Crack in the Crystal"

00:00 Welcome and Guest Intro

01:31 Origin of EAmmune Name

02:39 Resilience and Career Overview

04:51 Fractional CISO and Context Switching

06:38 Jessica Burnout Story

08:39 Lightning Angel Name Meaning

09:10 Relationships Over Everything

11:58 Bankruptcy and Customer Lifeline

15:15 Bootstrapping and Early Hustle

17:38 Strengths Focus and Delegation

19:33 Leaving Corporate and Forced Independence

22:34 Referral Growth Philosophy

23:58 Radical Transparency

24:59 Accidental Career Path

25:56 Reputation Compounds

28:12 Resilience Over Perfection

30:53 Trust Beats Skill

32:43 Owning Mistakes

34:39 Pretty Little Princess

36:04 Practice Context Switching

39:11 Humility and Humanity

43:00 Books and Farewell

From Bartending to COO: Hospitality Skills, Remote Work, and Critical Thinking in Cybersecurity

The host welcomes Alise Barron to the Cybersecurity Recruiter podcast and introduces her career path from hospitality and internet marketing into recruiting leadership roles at Experis Finance, Cylance, and Blackberry, and then multiple promotions at Cyvatar to COO.

Elise describes a typical remote-work day balancing family routines, early email catch-up due to time zones, constant meetings, and handling unexpected escalations in cybersecurity operations. They discuss why hospitality backgrounds can drive rapid advancement: strong work ethic, quick critical thinking, customer and stakeholder management, resilience, and learning to set boundaries without adopting a victim mindset. Elise connects these skills to project management, noting she later recognized she had been applying PMP-style practices.

They also discuss productivity tradeoffs between remote and office work, the value of networking, and how incident response requires structure, patience, and calm communication.

00:00 Welcome and Catch Up

00:42 Small World in Security

01:47 Elise Career Intro

02:59 COO Daily Routine

04:58 Remote Work Realities

08:44 From Bartender to COO

13:39 Hospitality Skills in Corporate

18:02 Boundaries and Ownership

19:24 Project Management Mindset

25:12 Hiring Through Networking

26:59 AI and Recruiting Filters

29:20 Closing Thoughts and Wrap